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PubMed2005

Self-assembly of dialkyltin moieties and mercaptobenzoic acid into macrocyclic complexes with hydrophobic "pseudo-cage" or double-cavity structures: supramolecular infrastructures involving intermolecular C-H...S weak hydrogen bonds and pi-pi interactions.

Four novel organotin complexes of two types--[R2Sn(o-SC6H4CO2)]6 (R = Me, 1 x H2O; nBu, 2) and {[R2Sn(m-CO2C6H4S)R2Sn(m-SC6H4CO2)SnR2]O}2 (R = Me, 3; nBu, 4)--have been prepared by treatment of o- or m-mercaptobenzoic acid and the corresponding R2SnCl2 (R = Me, nBu) with sodium ethoxide in ethanol (95%). All the complexes were characterized by elemental analysis, FT-IR and NMR (1H, (3C, 119Sn) spectroscopy, TGA, and X-ray crystallography diffraction analysis. The molecular structure analyses reveal that both 1 and 2 are hexanuclear macrocycles with hydrophobic "pseudo-cage" structures, while 3 and 4 are hexanuclear macrocycles with double-cavity structures. Furthermore, the supramolecular structure analyses show that looser and more intriguing supramolecular infrastructures were also found in complexes 1-4, which exist either as one-dimensional chains of rings or as two-dimensional networks assembled from the organometallic subunits through intermolecular C-H...S weak hydrogen bonds (WHBs) and pi-pi interactions.

Crystallography, X-Ray↗
PubMed2003

Biodegradation during contaminant transport in porous media: 6. Impact of sorption on coupled degradation-transport behavior.

Bioavailability is one of the critical factors influencing the biodegradation and bioremediation of organic compounds. The bioavailability of many organic contaminants is controlled in part by the nature, magnitude, and rate of sorption/desorption processes. This study investigates the impact of sorption and associated retardation on the bioavailability and biodegradation of aromatic hydrocarbons during transport in porous media. Miscible-displacement experiments were conducted using naphthalene and 2-naphthol as the model sorbing compounds and salicylate, a degradation product of naphthalene, as a nonsorbing reference compound. Two porous media were used, one (Eustis soil, FL, USA) with moderate sorption capacity and one (quartz sand) with no measurable sorption of the compounds. The porous media were sterilized and inoculated with Pseudomonas putida RB1353, an organism that degrades naphthalene and its derivatives. The biodegradation and transport of all three substrates in quartz sand were significantly influenced by microbial lag, the effects of which were observed within two to three pore volumes (3-4.5 h). This was also true for salicylate transport in the Eustis soil system. Conversely, biodegradation lag effects were not observed for naphthalene or 2-naphthol in the Eustis soil system. In addition, the masses of naphthalene and 2-naphthol degraded were significantly greater for the Eustis soil system compared to the quartz sand system. As noted previously, naphthalene and 2-naphthol were sorbed by the Eustis soil but not the quartz sand, while salicylate was not sorbed by either media. These results indicate that the increased residence time associated with sorption of naphthalene and 2-naphthol by Eustis soil enhanced overall biodegradation and obviated the impact of lag on observed transport behavior.

Adsorption↗
PubMed2006

Synthesis of beta-hydroxypropanoic acid derivatives as potential anti-inflammatory, analgesic and antimicrobial agents.

A series of new 3-(substituted) 3-hydroxy-propanoic acid ethyl esters 1a-c, hydrazides 2a-c, thiosemicarbazides 3a-f, and semicarbazides 3g, 3h has been synthesized. Cyclization of compounds 3a-d in basic medium yielded 1,2,4-triazole-5-thiones 4a-d. On the other hand, reaction of hydrazides 2a-c with CS(2 )in basic medium afforded 1,3,4-oxadiazole-5-thiones 5a-c. All the synthesized compounds were characterized by their physical and spectral analyses data. The newly synthesized compounds were evaluated for their anti-inflammatory, analgesic, and antimicrobial activities. Compounds 1c, 3g, 4a, 4b, 4c, and 5c exhibited comparable anti-inflammatory activity to that of indomethacin and compounds 1c, 4c, and 5c were more analgesics than acetyl salicylic acid. Compounds 4b, 4c, and 5c showed superior GI safety profile (33.3%, 33.3% and 50.0% ulceration) than that of indomethacin (100% ulceration) at 100 mg/kg oral dose. Compounds 4b, 4c, and 5c were also non-toxic with a median lethal dose (LD(50)) up to 200 mg/kg. The antibacterial and antifungal screenings identified compounds 3c, 4b, 4d, 5a, and 5b as the most effective against a variety of tested microorganisms.

Analgesics↗
PubMed1994

Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers.

The action of the phenolic compounds acetaminophen, salicylate, and 5-aminosalicylate (5-ASA) as inhibitors of lipid peroxidation was studied under conditions suitable for establishing their antioxidant potencies. These phenolic compounds react differently with diphenylpicrylhydrazyl (DPPH) and protect differently sarcoplasmic reticulum membranes against lipid peroxidation induced by Fe2+/ascorbate, as evaluated by the formation of thiobarbituric acid-reactive substances (TBARS) and by the loss of the polyunsaturated fatty acyl chains. 5-Aminosalicylate reacts promptly with DPPH, suggesting a potent radical scavenger activity and was found to be the most active in inhibiting Fe2+/ascorbate-induced lipid peroxidation. These compounds also exhibit peroxyl radical scavenging activity generated by the water-soluble 2,2'-azobis-(2-amidinopropane hydrochloride) azoinitiator of peroxyl radicals, as evidenced by the inhibition of cis-parinaric acid fluorescence decay or oxygen consumption. 5-ASA rapidly scavenges peroxyl radicals in the aqueous phase, producing a concentration-dependent inhibition period similar to Trolox or cysteine, suggesting an antioxidant activity of chain-breaking type. By comparison, the reactivities of acetaminophen and salicylate are significantly weaker, acting essentially as oxidation retardants. Although closely related in structure, the antioxidant efficiencies of the three phenolic compounds are significantly different. The higher antioxidant activity of 5-ASA is putatively related with the p-amine relative to the hydroxyl group, potentially increasing the stability of the phenoxyl radical. Such a stabilization is not possible with salicylate and is decreased in acetaminophen by an electron withdrawing effect of the p-acetyl.

Acetaminophen↗
PubMed2006

Fragrance of Canada thistle (Cirsium arvense) attracts both floral herbivores and pollinators.

The evolution of floral scent as a plant reproductive signal is assumed to be driven by pollinator behavior, with little attention paid to other potential selective forces such as herbivores. I tested 10 out of the 13 compounds emitted by dioecious Cirsium arvense, Canada thistle, including 2-phenylethanol, methyl salicylate, p-anisaldehyde, benzaldehyde, benzyl alcohol, phenylacetaldehyde, linalool, furanoid linalool oxides (E and Z), and dimethyl salicylate. Single compounds (and one isomer) set out in scent-baited water-bowl traps trapped over 10 species of pollinators and 16 species of floral herbivores. The two dominant components of the fragrance blend of C. arvense, benzaldehyde and phenylacetaldehyde, trapped both pollinators and florivores. Other compounds attracted either pollinators or florivores. Florivores of C. arvense appear to use floral scent compounds as kairomones; by advertising to pollinators, C. arvense also attracts its own enemies.

Acetaldehyde↗
PubMed2001

Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.

Acetylsalicylic acid (Aspirin) is rapidly metabolized to salicylic acid (salicylate) and other compounds, including gentisic acid and salicyluric acid. Monitoring of salicylate and its metabolites is of toxicological, pharmacological and biomedical interest. Three capillary electrophoresis (CE) methods featuring alkaline aqueous buffers, laser-induced fluorescence (LIF) detection and no solute extraction or derivatization have been explored. A competitive binding, electrokinetic capillary-based immunoassay is developed that recognizes the presence of salicylate and gentisic acid in urine. Differentiation of the two compounds, however, is problematic. With appropriate ultraviolet excitation, many salicylate-related compounds are fluorescent so that CE with direct urine injection and LIF detection permits the determination of salicylate, gentisic acid and salicyluric acid. Using a HeCd laser with 325 nm produces interference-free monitoring of all three compounds. Using 257 nm excitation from a frequency doubled Ar ion laser, native fluorescence of an endogenous urinary compound that co-migrates with gentisic acid is observed. With wavelength-resolved fluorescence detection, however, the two substances are distinguished. Furthermore, this technique, with comparison to literature data, permits the putative assignment of several peaks to other salicylate metabolites, namely glucuronide conjugates of salicylate and salicyluric acid. All three CE-LIF techniques have been applied to toxicological patient urines and urines collected after ingestion of 500 mg acetylsalicylic acid. CE results compare favorably with those obtained by a commercial fluorescence polarization immunoassay and by a conventional photometric assay.

Aspirin↗